Morpholine → (4-(4-Methylpiperidin-1-yl)-3-nitrophenyl)methanol

HRID 33469Notes

Reaction equation

HRID 33469 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH3:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.N1CCOCC1>C(Cl)(Cl)Cl>[CH3:13][CH:14]1[CH2:19][CH2:18][N:17]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 693814-MethylpiperidineHCID 41675874-Fluoro-3-nitrobenzyl alcohol

Product 1

HCID 28963353(4-(4-Methylpiperidin-1-yl)-3-nitrophenyl)methanol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

A stirred suspension of (4-fluoro-3-nitro-phenyl)-methanol (171 mg, 1 mmol), 4-methyl piperidine (95 mg, 0.96 mmol) PS morpholine (400 mg, 1 mmol), and chloroform (3 mL) was heated at 50° C. for 2 hrs. The reaction was evaporated onto celite and purified by flash chromatography to give [4-(4-methyl-piperidin-1-yl)-3-nitro-phenyl]-methanol (i). 1H NMR (CDCl3, 300 MHz): δ 7.8 (s, 1H), 7.4 (d, 1H), 7.1 (d, 1H), 4.6 (s, 2H), 3.2 (d, 2H), 2.8 (dd, 2H), 1.8-1.3 (m, 5H), 1.0 (d, 3H).

Workup

  1. customThe reaction was evaporated onto celite
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-ee91f2fb4d5d444dba1ba278f1df6b08
Source dataset
uspto-grants-2008_09
Patent number
US07429603B2

Reaction notes

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